#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:47:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180316 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/30/7153027.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153027
loop_
_publ_author_name
'Goel, Atul'
'Taneja, Gaurav'
'Raghuvanshi, Ashutosh'
'Kant, Ruchir'
'Maulik, Prakas R.'
_publ_section_title
;
 Diversity-oriented general protocol for the synthesis of privileged
 oxygen scaffolds: pyrones, coumarins, benzocoumarins and
 naphthocoumarins.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5239
_journal_page_last               5253
_journal_paper_doi               10.1039/c3ob40859k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C12 H6 Cl2 N4 O2'
_chemical_formula_sum            'C12 H6 Cl2 N4 O2'
_chemical_formula_weight         309.11
_chemical_melting_point          241
_chemical_name_common            Benzofuran
_chemical_name_systematic
;
3-amino-6,7-dichloro-5-hydroxybenzofuran-2,4-dicarbonitrile
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.5930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.542(2)
_cell_length_b                   7.5120(10)
_cell_length_c                   18.182(2)
_cell_measurement_reflns_used    1471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4553
_cell_measurement_theta_min      3.2686
_cell_volume                     2643.2(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_molecular_graphics    'SHELXTL-NT(Bruker, 1997)'
_computing_publication_material  'SHELXTL-NT(Bruker, 1997)'
_computing_structure_refinement  'SHELXTL-NT(Bruker, 1997)'
_computing_structure_solution    'SHELXTL-NT(Bruker, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0938
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8334
_diffrn_reflns_theta_full        32.53
_diffrn_reflns_theta_max         32.53
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0668P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                2448
_reflns_number_total             4295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40859k.txt
_cod_data_source_block           *****
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'Constr' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7153027
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C2 C 0.85204(12) 0.1105(3) 0.00149(14) 0.0371(6) Uani 1 1 d .
C3 C 0.90209(11) 0.1889(3) 0.06264(14) 0.0339(5) Uani 1 1 d .
C4 C 1.02411(11) 0.3016(3) 0.06503(13) 0.0307(5) Uani 1 1 d .
C5 C 1.06555(11) 0.3179(3) 0.01756(13) 0.0335(5) Uani 1 1 d .
C6 C 1.04014(11) 0.2585(3) -0.06059(14) 0.0336(5) Uani 1 1 d .
C7 C 0.97545(11) 0.1819(3) -0.09183(13) 0.0318(5) Uani 1 1 d .
C8 C 0.93517(10) 0.1677(3) -0.04409(13) 0.0307(5) Uani 1 1 d .
C9 C 0.95774(10) 0.2269(3) 0.03253(12) 0.0296(5) Uani 1 1 d .
C10 C 0.78684(12) 0.0444(4) -0.00304(15) 0.0442(6) Uani 1 1 d .
C11 C 1.04967(12) 0.3646(4) 0.14407(14) 0.0384(6) Uani 1 1 d .
C13 C 0.74450(16) 0.3375(5) 0.7614(2) 0.0663(9) Uani 1 1 d .
C14 C 0.7731(2) 0.3351(6) 0.6990(2) 0.0783(11) Uani 1 1 d .
H14A H 0.8031 0.2340 0.7051 0.117 Uiso 1 1 calc R
H14B H 0.7990 0.4423 0.7006 0.117 Uiso 1 1 calc R
H14C H 0.7364 0.3274 0.6498 0.117 Uiso 1 1 calc R
Cl1 Cl 0.94464(4) 0.10260(10) -0.18560(4) 0.0487(2) Uani 1 1 d .
Cl2 Cl 1.09143(3) 0.28719(11) -0.11730(4) 0.0517(2) Uani 1 1 d .
N1 N 0.73479(11) -0.0094(4) -0.00312(14) 0.0619(7) Uani 1 1 d .
N2 N 0.90134(11) 0.2194(3) 0.13548(13) 0.0488(6) Uani 1 1 d .
H6A H 0.8661 0.1881 0.1480 0.059 Uiso 1 1 calc R
H6B H 0.9361 0.2702 0.1694 0.059 Uiso 1 1 calc R
N3 N 1.06813(13) 0.4134(3) 0.20684(13) 0.0562(7) Uani 1 1 d .
N4 N 0.72296(19) 0.3340(6) 0.8104(2) 0.1065(13) Uani 1 1 d .
O1 O 0.87109(8) 0.0952(2) -0.06558(9) 0.0364(4) Uani 1 1 d .
O2 O 1.12813(9) 0.3912(3) 0.05090(10) 0.0480(5) Uani 1 1 d .
H3 H 1.1496 0.3880 0.0202 0.072 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C2 O1 112.85(19)
C3 C2 C10 129.9(2)
O1 C2 C10 117.2(2)
N2 C3 C2 128.1(2)
N2 C3 C9 127.3(2)
C2 C3 C9 104.5(2)
C5 C4 C9 118.5(2)
C5 C4 C11 119.5(2)
C9 C4 C11 121.97(19)
O2 C5 C4 116.4(2)
O2 C5 C6 124.00(19)
C4 C5 C6 119.6(2)
C7 C6 C5 121.65(19)
C7 C6 Cl2 120.27(18)
C5 C6 Cl2 118.07(17)
C6 C7 C8 117.8(2)
C6 C7 Cl1 122.44(16)
C8 C7 Cl1 119.73(17)
O1 C8 C9 112.57(18)
O1 C8 C7 125.1(2)
C9 C8 C7 122.3(2)
C8 C9 C4 120.01(18)
C8 C9 C3 106.00(19)
C4 C9 C3 134.0(2)
N1 C10 C2 176.9(3)
N3 C11 C4 178.0(3)
N4 C13 C14 177.8(5)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C3 N2 H6A 120.0
C3 N2 H6B 120.0
H6A N2 H6B 120.0
C8 O1 C2 104.08(17)
C5 O2 H3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 C3 1.369(3)
C2 O1 1.405(3)
C2 C10 1.405(3)
C3 N2 1.349(3)
C3 C9 1.452(3)
C4 C5 1.406(3)
C4 C9 1.408(3)
C4 C11 1.435(3)
C5 O2 1.342(3)
C5 C6 1.412(3)
C6 C7 1.383(3)
C6 Cl2 1.717(2)
C7 C8 1.390(3)
C7 Cl1 1.714(2)
C8 O1 1.355(2)
C8 C9 1.386(3)
C10 N1 1.143(3)
C11 N3 1.136(3)
C13 N4 1.120(4)
C13 C14 1.443(5)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N2 H6A 0.8600
N2 H6B 0.8600
O2 H3 0.8200
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C2 C3 N2 -178.1(2)
C10 C2 C3 N2 1.3(5)
O1 C2 C3 C9 0.0(3)
C10 C2 C3 C9 179.4(3)
C9 C4 C5 O2 179.4(2)
C11 C4 C5 O2 0.9(3)
C9 C4 C5 C6 -0.5(3)
C11 C4 C5 C6 -179.0(2)
O2 C5 C6 C7 179.2(2)
C4 C5 C6 C7 -0.9(4)
O2 C5 C6 Cl2 -1.8(3)
C4 C5 C6 Cl2 178.07(19)
C5 C6 C7 C8 1.2(4)
Cl2 C6 C7 C8 -177.76(19)
C5 C6 C7 Cl1 -177.93(19)
Cl2 C6 C7 Cl1 3.2(3)
C6 C7 C8 O1 -179.5(2)
Cl1 C7 C8 O1 -0.4(3)
C6 C7 C8 C9 -0.1(4)
Cl1 C7 C8 C9 179.01(18)
O1 C8 C9 C4 178.3(2)
C7 C8 C9 C4 -1.2(4)
O1 C8 C9 C3 -0.3(3)
C7 C8 C9 C3 -179.8(2)
C5 C4 C9 C8 1.5(3)
C11 C4 C9 C8 -180.0(2)
C5 C4 C9 C3 179.6(3)
C11 C4 C9 C3 -1.9(4)
N2 C3 C9 C8 178.3(2)
C2 C3 C9 C8 0.2(3)
N2 C3 C9 C4 0.0(5)
C2 C3 C9 C4 -178.1(3)
C3 C2 C10 N1 -17(6)
O1 C2 C10 N1 163(6)
C5 C4 C11 N3 176(9)
C9 C4 C11 N3 -3(9)
C9 C8 O1 C2 0.3(3)
C7 C8 O1 C2 179.8(2)
C3 C2 O1 C8 -0.1(3)
C10 C2 O1 C8 -179.7(2)
